8 Great Movies About Being Single

This stellar cast includes the late, great Whitney Houston, along with Angela Bassett, Loretta Divine, and Lela Rochon. These four friends deal with the slings and arrows of romance (or the lack thereof): cheating partners, raising families, and of course, setting cars on fire. The film was actually adapted from the 1992 novel of the same name by Terry McMillan. The story is centered in Phoenix, Arizona as the four leads are "holding their breath" until they can find a committed relationship with a man. The film, which was directed by Oscar-winning actor Forest Whitaker, features a smash-hit soundtrack by Babyface. It is refreshing in its array of relationships and its range of interactions. The heart-wrenching performances still hold up more than 20 years after the film’s release. So go ahead hit play and get ready to feel empowered; your confidence will skyrocket! 

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After being unceremoniously dumped for younger women by their husbands, three middle-aged women and former best friends, Annie (Diane Keaton), Elise (Goldie Hawn), and Brenda (Bette Midler), launch a full-scale attack of sweet, sweet revenge. Encouraged by their former friend—Cynthia Swann—the women form the First Wives Club after feeling that they have been taken granted by their husbands. They dig up dirt on their husbands and all hell breaks lose. These three powerhouse actresses made First Wives Club an absolute classic, and gave new life to the Lesley Gore song “You Don’t Own Me.” Fur? Check! Pearls? Check! Champagne? Check! Revenge has never looked so classy.

This movie, based on the wildly (pardon the pun) popular memoir by Cheryl Strayed, focuses on Cheryl’s odyssey to hike the Pacific Crest Trail on her own. Cheryl leaves Minneapolis, Minnesota without any hiking experience. Grieving the death of her mother, recently divorced, and struggling with addiction, Cheryl (played by Reese Witherspoon) pushes her body and spirit to the limit to prove she can face this challenge and much more. During the hike, Cheryl reflects through flashbacks on her childhood in Minnesota and memories of her mother, Bobbi Grey. Along the way, she experiences the healing she was so desperately searching for. This is relatable story of failure, mistakes, mourning, and rising in order to carry on throughout life. A great movie to feel a little less lonely as you search for who you really are.

It’s hard to get more quintessentially 90s than Reality Bites, the tale of four college friends trying to make their way in the world. The film stars Winona Ryder as Lelaina Pierce, a filmmaker fighting her attraction to bad boy musician Troy Dyer (Ethan Hawke at his Hawke-iest) while trying to build a career and a life for herself. Lelaina is working on a documentary called—you guessed it!—Reality Bites about the marginalized lives of her roommates. Lelaina's best friend Vickie (played with perfection by Janeane Garofalo) is a dedicated single lady, while Sammy (Steve Zahn) is a gay man struggling to come out to his conservative family. Together these four young people represent the best and worst of what it meant to be single in the late 90s. The film did a great job of capturing some of the career and lifestyle choices young Americans faced during the early 90s. With the perfect 80s and 90s indie soundtrack and grunge fashion, it is definitely worth the nostalgic trip down memory lane! 

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Based on the popular book by Ann Brashares, The Sisterhood of the Traveling Pants is a celebration of young womanhood and the friendships that see us through it. The film stars Amber Tamblyn, Alexis Bledel, Blake Lively, and America Ferrera, otherwise known as the It Girls of the early aughts, and follows four best friends on their first summer apart. They share a pair of precious denim, which somehow fits all of them perfectly, despite being different shapes and sizes. It unites the friends as they start off different directions in their lives. The jeans serve as a physical reminder of the connection between them all, and gives them the courage to face things like grief, parental disappointment, and first love. Each girl has a distinct personality and interesting stories as each deals with changes and growing up. So grab your tissues because one is a real tearjerker!

The cast of this 2000 film would soon be big names on television and film, including Zack Braff, Timothy Olyphant, and Justin Theroux. But in Broken Hearts Club, they are just a group of gay guys trying to find a little happiness. This crew of West Hollywood single gay men is looking for love in all the wrong places, and their bond is anchored by their patriarch of sorts, Jack (the legendary late John Mahoney). This film received praise for portraying homosexuality as normal and its characters as average gay men. It also focuses on universal themes of love, acceptance, and family. The film picked up a GLAAD Award for Best Feature and is one of the first major films to take place after medical advances began turning the tide for those affected by HIV and AIDS. At the core, it emphasizes the beautiful friendship that they share in order to support each other in their struggles—it'll make you send your friend a heart emoji or two. 

This Judd Apatow-produced movie ultimately has a happily-ever-after for its lead, but most of the movie is devoted to protagonist Peter (Jason Segel) hilariously finding himself after an abrupt ending to a five-year relationship. When Peter's actress girlfriend Sarah Marshall (Kristen Bell) leaves him for rockstar Aldous Snow (Russell Brand), Peter is devastated. He tries to escape his feelings by taking a vacation in Hawaii, only to find that Sarah and Aldous are at the same resort. Peter is inconsolable, but with the help of generous concierge Rachel (Mila Kunis) he gains some perspective about the breakup and grows more excited for the personal projects he can explore now that Sarah is out of his life. It is so relatable as some of us have to face that awkward and difficult scenario of seeing an ex-lover moving on. It is a comedy full of heart and we will make literally laugh out loud! 

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This painfully underrated film about being a free spirit stars Uma Thurman as Sissy Hankshaw, a woman with a talent for hitchhiking and blessed with unusually large thumbs. As you can imagine, the two go hand in hand. As Sissy goes on her travels she learns about various topics: homosexuality, free love, drug use, political rebellion, animal rights, and religions. Sissy might be a loner, but she’s not lonely, making friends and admirers wherever she goes. She’s always happier on the road, and her magical thumbs take her to places she never even imagined and introduce her to people who will change her life forever. Her travels lead her to New York, where she becomes a model for a mogul, known as The Countess. The film presents American counterculture and 70s value that are still important like the search for sexual identity. The k.d. lang soundtrack is worth a viewing alone. So grab onto your hats, this is going to be a bumpy ride!